JPS6044523A - ノルボルニル変性ポリエステルアミドおよびその製造法 - Google Patents
ノルボルニル変性ポリエステルアミドおよびその製造法Info
- Publication number
- JPS6044523A JPS6044523A JP58149708A JP14970883A JPS6044523A JP S6044523 A JPS6044523 A JP S6044523A JP 58149708 A JP58149708 A JP 58149708A JP 14970883 A JP14970883 A JP 14970883A JP S6044523 A JPS6044523 A JP S6044523A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkylene
- norbornene
- diamine
- bonded
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920006149 polyester-amide block copolymer Polymers 0.000 title claims abstract description 76
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000004985 diamines Chemical class 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 50
- 229920005862 polyol Polymers 0.000 claims abstract description 22
- 150000003077 polyols Chemical class 0.000 claims abstract description 21
- -1 norbornene compound Chemical class 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 229910001868 water Inorganic materials 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 40
- 239000012141 concentrate Substances 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 229920000728 polyester Polymers 0.000 claims description 29
- 238000007792 addition Methods 0.000 claims description 28
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
- 150000002848 norbornenes Chemical class 0.000 claims description 13
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- 229920006305 unsaturated polyester Polymers 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000539 dimer Substances 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims 4
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 claims 2
- 229930185605 Bisphenol Natural products 0.000 claims 1
- 235000014676 Phragmites communis Nutrition 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005263 alkylenediamine group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000004984 aromatic diamines Chemical class 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims 1
- 125000004031 fumaroyl group Chemical group C(\C=C\C(=O)*)(=O)* 0.000 claims 1
- 125000003099 maleoyl group Chemical group C(\C=C/C(=O)*)(=O)* 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims 1
- 229920005903 polyol mixture Polymers 0.000 claims 1
- 230000007797 corrosion Effects 0.000 abstract description 21
- 238000005260 corrosion Methods 0.000 abstract description 21
- 230000008569 process Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 39
- 230000008859 change Effects 0.000 description 29
- VQVUBYASAICPFU-UHFFFAOYSA-N (6'-acetyloxy-2',7'-dichloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(OC(C)=O)C=C1OC1=C2C=C(Cl)C(OC(=O)C)=C1 VQVUBYASAICPFU-UHFFFAOYSA-N 0.000 description 28
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 27
- 229920000180 alkyd Polymers 0.000 description 24
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000007062 hydrolysis Effects 0.000 description 19
- 238000006460 hydrolysis reaction Methods 0.000 description 19
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002009 diols Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000005266 casting Methods 0.000 description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 238000005452 bending Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 230000009435 amidation Effects 0.000 description 8
- 238000007112 amidation reaction Methods 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 229920001567 vinyl ester resin Polymers 0.000 description 8
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
- 230000020169 heat generation Effects 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 229920002799 BoPET Polymers 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 239000005041 Mylar™ Substances 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 3
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000010421 standard material Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- PMJHHCWVYXUKFD-PLNGDYQASA-N (3z)-penta-1,3-diene Chemical compound C\C=C/C=C PMJHHCWVYXUKFD-PLNGDYQASA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 102100028672 C-type lectin domain family 4 member D Human genes 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 101000766905 Homo sapiens C-type lectin domain family 4 member D Proteins 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- YFOOLJCLFKACPF-UHFFFAOYSA-N [3-(aminomethyl)-2-bicyclo[2.2.1]hept-2-enyl]methanamine Chemical compound C1CC2C(CN)=C(CN)C1C2 YFOOLJCLFKACPF-UHFFFAOYSA-N 0.000 description 1
- RDCRVCNPGSYUCY-UHFFFAOYSA-N [4-(hydroxymethyl)-3-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2(CO)C(CO)CC1C2 RDCRVCNPGSYUCY-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyamides (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/333,221 US4410686A (en) | 1981-12-21 | 1981-12-21 | Norbornyl modified polyesteramides and process for preparing same |
| US46572783A | 1983-02-11 | 1983-02-11 | |
| EP83107795A EP0134263B1 (en) | 1981-12-21 | 1983-08-08 | Norbornyl modified polyesteramides and process for preparing same |
| US06/548,746 US4471101A (en) | 1981-12-21 | 1983-11-04 | Norbornyl modified polyesteramides and process for preparing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6044523A true JPS6044523A (ja) | 1985-03-09 |
| JPH0337572B2 JPH0337572B2 (enrdf_load_stackoverflow) | 1991-06-06 |
Family
ID=36782516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58149708A Granted JPS6044523A (ja) | 1981-12-21 | 1983-08-18 | ノルボルニル変性ポリエステルアミドおよびその製造法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4410686A (enrdf_load_stackoverflow) |
| EP (1) | EP0134263B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS6044523A (enrdf_load_stackoverflow) |
| AT (1) | ATE29894T1 (enrdf_load_stackoverflow) |
| AU (1) | AU560766B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1211887A (enrdf_load_stackoverflow) |
| DE (1) | DE3373820D1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02102909A (ja) * | 1988-10-06 | 1990-04-16 | Sanyo Electric Co Ltd | 冷蔵庫等の把手取付装置 |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5506060A (en) | 1981-11-13 | 1996-04-09 | The Boeing Company | Method for making multidimensional ether or ester oligomers |
| US5516876A (en) | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5512676A (en) | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5714566A (en) | 1981-11-13 | 1998-02-03 | The Boeing Company | Method for making multiple chemically functional oligomers |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| US4410686A (en) * | 1981-12-21 | 1983-10-18 | The Dow Chemical Company | Norbornyl modified polyesteramides and process for preparing same |
| WO1985001948A1 (en) * | 1983-10-24 | 1985-05-09 | The Dow Chemical Company | Polyesteramide concrete |
| US4560768A (en) * | 1983-12-16 | 1985-12-24 | The Dow Chemical Company | Polyimido-ester compounds and thermoset resin compositions containing same |
| US4587293A (en) * | 1984-02-24 | 1986-05-06 | The Dow Chemical Company | Reactive flexibilizing monomer and thermosettable compositions containing same |
| US4611015A (en) * | 1984-12-13 | 1986-09-09 | The Dow Chemical Company | Polymer concrete compositions containing water absorbent polymers |
| US4777209A (en) * | 1984-12-21 | 1988-10-11 | The Dow Chemical Company | Compositions of polycycloalkenyl-terminated, unsaturated polyesters or polyesteramides and vinyl-reactive plasticizers therefor |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US4594408A (en) * | 1985-07-15 | 1986-06-10 | The Dow Chemical Company | Unsaturated polyester (amide)s containing thiabicyclononane groups |
| AU6504886A (en) * | 1985-11-18 | 1987-05-21 | Dow Chemical Company, The | Polymer concrete |
| US4777196A (en) * | 1986-01-27 | 1988-10-11 | The Dow Chemical Company | Polymer modified unsaturated polyester or polyesteramide resins |
| AU592622B2 (en) * | 1986-01-27 | 1990-01-18 | Dow Chemical Company, The | Polymer modified unsaturated resin |
| US4777208A (en) * | 1986-01-27 | 1988-10-11 | The Dow Chemical Company | Polymer modified unsaturated polyester for polyesteramide resin polymer concrete |
| US4750374A (en) * | 1986-10-16 | 1988-06-14 | Hercules Incorporated | Process and apparatus for monitoring laminate structural stability |
| US4789602A (en) * | 1987-09-28 | 1988-12-06 | Eastman Kodak Company | Hydroxyethylnorbornene compounds and a process for their preparation |
| US4855395A (en) * | 1987-09-28 | 1989-08-08 | Eastman Kodak Company | Hydroxyethylnorbornene compounds and a process for their preparation |
| US4895926A (en) * | 1987-09-28 | 1990-01-23 | Eastman Kodak Company | Hydroxyethylnorbornene compounds and a process for their preparation |
| US4874837A (en) * | 1988-01-11 | 1989-10-17 | Owens-Corning Fiberglas Corporation | Aminated hydroxylated polyester polyol resin and molding compositions comprised thereof |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5021004A (en) * | 1990-07-26 | 1991-06-04 | Amp Incorporated | Secondary latch for pin connector |
| US7977424B2 (en) * | 2001-08-13 | 2011-07-12 | Zoran Petrovic | Polymer concrete and method for preparation thereof |
| EP1919976A1 (en) * | 2005-08-29 | 2008-05-14 | Shell Internationale Research Maatschappij B.V. | Integrated process for the preparation of a polyester resin |
| US20090187003A1 (en) * | 2005-09-29 | 2009-07-23 | Yuji Eguchi | Thermosetting resin, thermosetting composition containing same, and molded product obtained from same |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1317598A (enrdf_load_stackoverflow) * | 1961-03-13 | 1963-05-08 | ||
| US3445482A (en) * | 1965-08-12 | 1969-05-20 | Universal Oil Prod Co | Bis(polyhalocycloalkene)dicarboxylic acids and derivatives thereof |
| GB1195902A (en) * | 1966-05-19 | 1970-06-24 | Union Carbide Corp | Flame-Retardant Halogenated Polyesters |
| US3660521A (en) * | 1969-11-28 | 1972-05-02 | Eastman Kodak Co | Polymeric compounds |
| US3715342A (en) * | 1970-09-15 | 1973-02-06 | Union Carbide Corp | Radiation-convertible norbornene polymers |
| US3745149A (en) * | 1971-09-29 | 1973-07-10 | Nasa | Preparation of polyimides from mixtures of monomeric diamines and esters of polycarboxylic acids |
| US3933757A (en) * | 1973-02-08 | 1976-01-20 | Scm Corporation | Dicyclopentadiene thermosetting polyester |
| JPS5645951B2 (enrdf_load_stackoverflow) * | 1973-05-21 | 1981-10-29 | ||
| IT1031921B (it) * | 1975-02-21 | 1979-05-10 | Snia Viscosa | Poliesterammidi insature metodo per la loro produzione e resine induribili prodotte con le dette poliesterammidi |
| US4307002A (en) * | 1976-09-16 | 1981-12-22 | Hoechst Aktiengesellschaft | Resin binders and process for preparing them |
| JPS6050382B2 (ja) * | 1979-07-24 | 1985-11-08 | 日本ゼオン株式会社 | 不飽和ポリエステル樹脂組成物 |
| US4248997A (en) * | 1979-07-30 | 1981-02-03 | Toyo Ink Manufacturing Co., Ltd. | Process for producing curable esterified alkyd resins |
| US4246367A (en) * | 1979-09-24 | 1981-01-20 | United States Steel Corporation | Dicyclopentadiene polyester resins |
| US4348499A (en) * | 1979-10-05 | 1982-09-07 | The Dow Chemical Company | Heat resistant low shrink polyester resins |
| US4410686A (en) * | 1981-12-21 | 1983-10-18 | The Dow Chemical Company | Norbornyl modified polyesteramides and process for preparing same |
| US4409371A (en) * | 1982-04-08 | 1983-10-11 | The Dow Chemical Company | Dicyclopentadiene modified polyesteramides containing endomethylenetetrahydrophthalyl functionality and process for preparing same |
-
1981
- 1981-12-21 US US06/333,221 patent/US4410686A/en not_active Expired - Fee Related
-
1983
- 1983-08-02 CA CA000433729A patent/CA1211887A/en not_active Expired
- 1983-08-04 AU AU17595/83A patent/AU560766B2/en not_active Ceased
- 1983-08-08 AT AT83107795T patent/ATE29894T1/de active
- 1983-08-08 EP EP83107795A patent/EP0134263B1/en not_active Expired
- 1983-08-08 DE DE8383107795T patent/DE3373820D1/de not_active Expired
- 1983-08-18 JP JP58149708A patent/JPS6044523A/ja active Granted
- 1983-11-04 US US06/548,746 patent/US4471101A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02102909A (ja) * | 1988-10-06 | 1990-04-16 | Sanyo Electric Co Ltd | 冷蔵庫等の把手取付装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0134263B1 (en) | 1987-09-23 |
| EP0134263A1 (en) | 1985-03-20 |
| US4471101A (en) | 1984-09-11 |
| JPH0337572B2 (enrdf_load_stackoverflow) | 1991-06-06 |
| US4410686A (en) | 1983-10-18 |
| AU560766B2 (en) | 1987-04-16 |
| CA1211887A (en) | 1986-09-23 |
| DE3373820D1 (en) | 1987-10-29 |
| AU1759583A (en) | 1985-02-07 |
| ATE29894T1 (de) | 1987-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6044523A (ja) | ノルボルニル変性ポリエステルアミドおよびその製造法 | |
| US4822849A (en) | Low shrink hybrid resins | |
| US3674727A (en) | Unsaturated polyesters | |
| US4486582A (en) | Reactive monomers and thermosettable compositions containing same | |
| US4443580A (en) | DCPD Modified polyester physical property improvement | |
| US4485220A (en) | Polyoxazoline modified unsaturated polyesteramides | |
| US4435530A (en) | Heat resistant resin composition | |
| FI86310B (fi) | Kompositioner av polycykloalkenylterminerade, omaettade polyestrar eller polyesteramider och vinylreaktiva mjukningsmedel foer dem. | |
| US4409371A (en) | Dicyclopentadiene modified polyesteramides containing endomethylenetetrahydrophthalyl functionality and process for preparing same | |
| US2902462A (en) | Polyester of a mixture of isomeric c10 dicarboxylic acids and process of making | |
| DK163878B (da) | Pulverformigt belaegningsmiddel og fremgangsmaade til fremstilling af en belaegning under anvendelse heraf | |
| US4447577A (en) | Emulsions of dicyclopentadiene containing polyesters | |
| US4551489A (en) | Emulsions of dicyclopentadiene containing polyesters | |
| NZ205127A (en) | Norbornyl modified polyesteramides and their preparation | |
| US4496688A (en) | Heat resistant polyester(amide) composition | |
| SU598569A3 (ru) | Способ получени отвержденной смолы | |
| NZ205126A (en) | Dicyclopentadiene modified polyesteramides and their preparation | |
| US4587293A (en) | Reactive flexibilizing monomer and thermosettable compositions containing same | |
| US3772229A (en) | Production of polyesteramides from aziridine salts | |
| JPH0466259B2 (enrdf_load_stackoverflow) | ||
| CA2017069A1 (en) | High reactivity thermosettable molding compositions containing 2-methyl-1,3-propanediol | |
| US4640957A (en) | Polyimido-ester compounds and thermoset resin compositions containing same | |
| Lochab et al. | Thermal behaviour of dendritic methacrylated polyesters | |
| JPH0789932A (ja) | エーテル結合を有する不飽和イミド系化合物とその製法及び該化合物を含む樹脂組成物 | |
| JP2003096193A (ja) | ポリエステル系エラストマーおよびその製造方法 |